2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole

Base Information

• Chemical Name: 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole
• CAS No.: 1443234-66-9
• Molecular Formula: C₄₇H₄₅N₃OS₅
• Molecular Weight: 828.224

Synonyms:2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole

Chemical Property of 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole

There total 5 articles about 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-(4-hexyl-5-iodothiophen-2-yl)thiazolo[5,4-d]thiazole (1443234-65-8) + (5-formylthiophen-2-yl)boronic acid → 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole (1443234-66-9)

Guidance literature:

With potassium fluoride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In methanol; toluene; at 70 ℃; for 0.333333h; Schlenk technique; Inert atmosphere; Microwave irradiation;

DOI:10.1002/ejoc.201201629

Reference yield:

2,5-bis(4-hexyl-5-iodothiophen-2-yl)thiazolo[5,4-d]thiazole → 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole (1443234-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water / 5 h / 90 °C / Schlenk technique; Inert atmosphere

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium fluoride / toluene; methanol / 0.33 h / 70 °C / Schlenk technique; Inert atmosphere; Microwave irradiation

With potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In methanol; water; toluene; 1: |Suzuki Coupling / 2: |Suzuki Coupling;

DOI:10.1002/ejoc.201201629

Reference yield:

3-hexylthiophene (1693-86-3) → 2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-[4-hexyl-5-(5-formylthiophen-2-yl)thiophen-2-yl]thiazolo[5,4-d]thiazole (1443234-66-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium / tetrahydrofuran; pentane / -78 °C / Schlenk technique; Inert atmosphere

1.2: -78 - 20 °C / Schlenk technique; Inert atmosphere

2.1: neat (no solvent) / 0.25 h / 180 °C / Microwave irradiation; Schlenk technique; Inert atmosphere

3.1: N-iodo-succinimide; acetic acid / chloroform / 40 °C / Schlenk technique; Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; water / 5 h / 90 °C / Schlenk technique; Inert atmosphere

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium fluoride / toluene; methanol / 0.33 h / 70 °C / Schlenk technique; Inert atmosphere; Microwave irradiation

With 2,2,6,6-tetramethyl-piperidine; potassium fluoride; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tert.-butyl lithium; sodium carbonate; acetic acid; In tetrahydrofuran; methanol; chloroform; water; toluene; pentane; 4.1: |Suzuki Coupling / 5.1: |Suzuki Coupling;

DOI:10.1002/ejoc.201201629

upstream raw materials:

2,5-bis(4-hexylthiophen-2-yl)thiazolo[5,4-d]thiazole

2-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]thiophen-2-yl}-5-(4-hexyl-5-iodothiophen-2-yl)thiazolo[5,4-d]thiazole

3-hexylthiophene

4-hexylthiophene-2-carbaldehyde

Downstream raw materials:

2-cyano-3-{5-[4-hexyl-2-(5-{4-hexyl-5-[4-(diphenylamino)phen-1-yl]-thiophen-2-yl}thiazolo[5,4-d]thiazol-2-yl)thiophen-5-yl]thiophen-2-yl}prop-2-enoic acid

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